U.S. patent application number 11/508055 was filed with the patent office on 2006-12-14 for parasiticide formulations suitable for dermal application.
Invention is credited to Hubert Dorn, Doris Hackemuller, Ulrich Heukamp, Terence Hopkins, Klemens Krieger, Richard Kujanek, Kirkor Sirinyan.
Application Number | 20060281792 11/508055 |
Document ID | / |
Family ID | 6535391 |
Filed Date | 2006-12-14 |
United States Patent
Application |
20060281792 |
Kind Code |
A1 |
Sirinyan; Kirkor ; et
al. |
December 14, 2006 |
Parasiticide formulations suitable for dermal application
Abstract
The present invention relates to formulations for the dermal
control of parasitic insects on animals, having the following
composition agonists or antagonists of the nicotinergic
acetylcholine receptors of insects in a concentration of from 1 to
20% by weight based on the overall weight of the formulation;
solvents from the group benzyl alcohol or optionally substituted
pyrrolidones in a concentration of at least 20% by weight based on
the overall weight of the formulation; if desired, further solvents
from the group consisting of cyclic carbonates or lactones in a
concentration of from 5.0 up to 80% by weight based on the overall
weight of the formulation; if desired, further auxiliaries from the
group thickeners, spreading agents, colorants, antioxidants,
propellants, preservatives, adhesives, emulsifiers, in a
concentration of from 0.025 up to 10% by weight based on the
overall weight of the formulation.
Inventors: |
Sirinyan; Kirkor; (Bergisch
Gladbach, DE) ; Dorn; Hubert; (Wuppertal, DE)
; Kujanek; Richard; (Koln, DE) ; Krieger;
Klemens; (Del. Magdalena Contreras, MX) ; Heukamp;
Ulrich; (Kurten, DE) ; Hackemuller; Doris;
(Dusseldorf, DE) ; Hopkins; Terence; (Taborine,
AU) |
Correspondence
Address: |
JEFFREY M. GREENMAN
BAYER PHARMACEUTICALS CORPORATION
400 MORGAN LANE
WEST HAVEN
CT
06516
US
|
Family ID: |
6535391 |
Appl. No.: |
11/508055 |
Filed: |
August 21, 2006 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
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|
10094212 |
Mar 8, 2002 |
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11508055 |
Aug 21, 2006 |
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09435271 |
Nov 5, 1999 |
6372765 |
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10094212 |
Mar 8, 2002 |
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08849259 |
Jun 2, 1997 |
6001858 |
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PCT/EP95/04667 |
Nov 27, 1995 |
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09435271 |
Nov 5, 1999 |
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Current U.S.
Class: |
514/355 |
Current CPC
Class: |
A01N 61/00 20130101;
A61P 33/14 20180101; A01N 51/00 20130101; Y10S 514/83 20130101;
A01N 2300/00 20130101; A01N 2300/00 20130101; A01N 25/02 20130101;
A01N 61/00 20130101; A01N 25/02 20130101; A01N 51/00 20130101; A01N
61/00 20130101; A01N 51/00 20130101 |
Class at
Publication: |
514/355 |
International
Class: |
A01N 43/40 20060101
A01N043/40 |
Foreign Application Data
Date |
Code |
Application Number |
Dec 9, 1994 |
DE |
P 44 43 888.5 |
Claims
1. Compositions for the dermal control of parasitic insects on
animals, characterized in that it contains agonists or antagonists
of the nicotinergic acetylcholine receptors of insects in a
concentration of from 1 to 20% by weight based on the overall
weight of the formulation; solvents from the group benzyl alcohol
or optionally substituted pyrrolidones in a concentration of at
least 20% by weight based on the overall weight of the formulation;
if desired, further solvents from the group consisting of cyclic
carbonates or lactones in a concentration of from 5.0 up to 80% by
weight based on the overall weight of the formulation; if desired,
further auxiliaries from the group thickeners, spreading agents,
colorants, antioxidants, propellants, preservatives, adhesives,
emulsifiers, in a concentration of from 0.025 up to 10% by weight
based on the overall weight of the formulation.
2. Process for the production of the compositions according to
claim 1, characterized in that the active substance is mixed with
the stated solvent(s), and the further auxiliaries are added if
desired.
Description
[0001] The present invention relates to formulations for the dermal
control of parasitic insects on animals by means of agonists or
antagonists of the nicotinergic acetylcholine receptors of
insects.
[0002] Agonists or antagonists of the nicotinergic acetylcholine
receptors of insects are known. They include the nicotinyl
insecticides and, very particularly, the chloronicotinyl
insecticides.
[0003] PCT application WO 93/24 002 discloses that certain
1-[N-(halo-3-pyridylmethyl)]-N-methylamino-1-alkylamino-2-nitroethylene
derivatives are suitable for systemic use against fleas in domestic
animals. According to WO 93/24 002, the nonsystemic--i.e.
dermal--mode of application is unsuitable for the control of fleas
on domestic animals.
[0004] New formulations for the dermal application of agonists or
antagonists of the nicotinergic acetylcholine receptors of insects
have now been found which are particularly suitable for dermal
control of parasitic insects, such as fleas, lice or flies, on
animals.
[0005] The formulations according to the invention have the
following composition: [0006] agonists or antagonists of the
nicotinergic acetylcholine receptors of insects in a concentration
of from 1 to 20% by weight based on the overall weight of the
formulation; [0007] solvents from the group benzyl alcohol or
optionally substituted pyrrolidones in a concentration of at least
20% by weight based on the overall weight of the formulation;
[0008] if desired, further solvents from the group consisting of
cyclic carbonates or lactones in a concentration of from 5.0 up to
80% by weight based on the overall weight of the formulation;
[0009] if desired, further auxiliaries from the group thickeners,
spreading agents, colorants, antioxidants, propellants,
preservatives, adhesives, emulsifiers, in a concentration of from
0.025 up to 10% by weight based on the overall weight of the
formulation.
[0010] Agonists or antagonists of the nicotinergic acetylcholine
receptors of insects are known, for example, from European
Offenlegungsschriften (European Published Applications) Nos. 464
830, 428 941, 425 978, 386 565, 383 091, 375 907, 364 844, 315 826,
259 738, 254 859, 235 725, 212 600, 192 060, 163 855, 154 178, 136
636, 303 570, 302 833, 306 696, 189 972, 455 000, 135 956, 471 372,
302 389; German Offenlegungsschriften (German Published
Specifications) Nos. 3 639 877, 3 712 307; Japanese
Offenlegungsschriften (Japanese Published Applications) Nos. 03 220
176, 02 207 083, 63 307 857, 63 287 764, 03 246 283, 04 9371, 03
279 359, 03 255 072, U.S. Pat. Nos. 5,034,524, 4,948,798,
4,918,086, 5,039,686, 5,034,404; PCT Applications Nos. WO 91/17
659, 91/4965; French Application No. 2 611 114; Brazilian
Application No. 88 03 621.
[0011] Express reference is hereby made to the compounds described
in these publications and to their preparation.
[0012] These compounds can be represented preferably by the general
formula (I) ##STR1##
[0013] in which [0014] R represents, hydrogen, optionally
substituted radicals from the group acyl, alkyl aryl, aralkyl,
heteroaryl or heteroarylalkyl; [0015] A represents a monofunctional
group from the series hydrogen, acyl, alkyl, aryl, or represents a
bifunctional group which is linked to the radical Z; [0016] E
represents an electron-withdrawing radical; [0017] X represents the
radicals --CH.dbd. or .dbd.N--, it being possible for the radical
--CH.dbd. instead of a H-atom to be linked to the radical Z; [0018]
Z represents a monofunctional group from the series alkyl, --O--R,
--S--R, ##STR2## [0019] or represents a bifunctional group which is
linked to the radical A or to the radical X
[0020] Particularly preferred compounds of the formula (I) are
those in which the radicals have the following meaning: [0021] R
represents hydrogen and represents optionally substituted radicals
from the series acyl, alkyl, aryl, aralkyl, heteroaryl,
heteroarylalkyl. [0022] Acyl radicals which may be mentioned are
formyl, alkylcarbonyl, arylcarbonyl, alkylsulphonyl, arylsulphonyl,
(alkyl)-(aryl)-phosphoryl, which may in turn be substituted. [0023]
As alkyl there may be mentioned C.sub.1-10-alkyl, especially
C.sub.1-4-alkyl, specifically methyl, ethyl, i-propyl, sec- or
t-butyl, which may in turn be substituted. [0024] As aryl there may
be mentioned phenyl, naphthyl, especially phenyl. [0025] As aralkyl
there may be mentioned phenylmethyl, phenethyl. [0026] As
heteroaryl there may be mentioned heteroaryl having up to 10 ring
atoms and N, O, S especially N as heteroatoms. Specifically there
may be mentioned thienyl, furyl, thiazolyl, imidazolyl, pyridyl,
benzothiazolyl, [0027] As heteroarylalkyl there may be mentioned
heteroarylmethyl, heteroarylethyl having up to 6 ring atoms and N,
O, S, especially N as heteroatoms. [0028] Substituents which may be
listed by way of example and preference are: alkyl having
preferably 1 to 4, in particular 1 or 2 carbon atoms, such as
methyl, ethyl, n- and i-propyl and n-, i- and t-butyl; alkoxy
having preferably 1 to 4, in particular 1 or 2 carbon atoms, such
as methoxy, ethoxy, n- and i-propyloxy and n-, i- and t-butyloxy;
alkylthio having preferably 1 to 4, in particular 1 or 2 carbon
atoms, such as methylthio, ethylthio, n- and i-propylthio and n-,
i- and t-butylthio; halogenoalkyl having preferably 1 to 4, in
particular 1 or 2 carbon atoms and preferably 1 to 5, in particular
1 to 3 halogen atoms, the halogen atoms being identical or
different and being preferably fluorine, chlorine or bromine,
especially fluorine, such as trifluoromethyl; hydroxyl; halogen,
preferably fluorine, chlorine, bromine and iodine, especially
fluorine, chlorine and bromine; cyano; nitro; amino; monoalkyl- and
dialkylamino having preferably 1 to 4, in particular 1 or 2 carbon
atoms per alkyl group, such as methylamino, methyl-ethyl-amino, n-
and i-propylamino and methyl-n-butylamino; carboxyl; carbalkoxy
having preferably 2 to 4, in particular 2 or 3 carbon atoms, such
as carbomethoxy and carboethoxy; sulpho (--SO.sub.3H);
alkylsulphonyl having preferably 1 to 4, in particular 1 or 2
carbon atoms, such as methylsulphonyl and ethylsulphonyl;
arylsulphonyl having preferably 6 or 10 aryl carbon atoms, such as
phenylsulphonyl, and also heteroarylamino and heteroarylalkylamino
such as chloropyridylamino and chloropyridylmethylamino. [0029] A
particularly preferably represents hydrogen and represents
optionally substituted radicals from the series acyl, alkyl, aryl,
which preferably have the meanings given for R. A additionally
represents a bifunctional group. There may be mentioned optionally
substituted alkylene having 1-4, in particular 1-2 C atoms,
substituents which may be mentioned being the substituents listed
earlier above, and it being possible for the alkylene groups to be
interrupted by heteroatoms from the series N, O, S. [0030] A and Z
may, together with the atoms to which they are attached, form a
saturated or unsaturated heterocyclic ring. The heterocyclic ring
can contain a further 1 or 2 identical or different heteroatoms
and/or hetero-groups. Heteroatoms are preferably oxygen, sulphur or
nitrogen, and hetero-groups are preferably N-alkyl, where the alkyl
in the N-alkyl group preferably contains 1 to 4, in particular 1 or
2 carbon atoms. As alkyl there may be mentioned methyl, ethyl, n-
and i-propyl and n-, i- and t-butyl. The heterocyclic ring contains
5 to 7, preferably 5 or 6 ring members. [0031] Examples of the
heterocyclic ring which may be mentioned are pyrrolidine,
piperidine, piperazine, hexamethyleneimine,
hexahydro-1,3,5-triazine, morpholine, each of which may optionally
be substituted preferably by methyl. [0032] E represents an
electron-withdrawing radical, in which context particular mention
may be made of NO.sub.2, CN, halogenoalkylcarbonyl such as
1,5-halogeno-C.sub.1-4-carbonyl especially COCF.sub.3. [0033] X
represents --CH.dbd. or --N.dbd. [0034] Z represents optionally
substituted radicals, alkyl, --OR, --SR, --NRR, where R and the
substituents preferably have the meaning given above. [0035] Z can
form, apart from the abovementioned ring, and together with the
atom to which it is attached and with the radical ##STR3## [0036]
instead of X, a saturated or unsaturated heterocyclic ring. The
heterocyclic ring can contain a further 1 or 2 identical or
different heteroatoms and/or hetero-groups. The heteroatoms are
preferably oxygen, sulphur or nitrogen, and the hetero-groups
N-alkyl, in which case the alkyl or N-alkyl group preferably
contains 1 to 4, in particular 1 or 2 carbon atoms. As alkyl there
may be mentioned methyl, ethyl, n- and i-propyl and n-, i- and
t-butyl. The heterocyclic ring contains 5 to 7, preferably 5 or 6
ring members. [0037] Examples of the heterocyclic ring which may be
mentioned are pyrrolidine, piperidine, piperazine,
hexamethyleneimine, morpholine and N-methylpiperazine.
[0038] As compounds which may be used with very particular
preference in accordance with the invention, mention may be made of
compounds of the general formulae (II) and (III): ##STR4## in which
[0039] n represents 1 or 2, [0040] subst. represents one of the
above-listed substituents, especially halogen, very particularly
chlorine, [0041] A, Z, X and E have the meanings given above,
[0042] Specifically, the following compounds may be mentioned:
##STR5## ##STR6## ##STR7##
[0043] The formulations according to the invention contain the
active substance in concentrations of from 0.1 to 20% by weight,
preferably from 1 to 12.5% by weight.
[0044] Preparations which are diluted before use contain the active
substance in concentrations of from 0.5 to 90% by weight,
preferably from 1 to 50% by weight.
[0045] In general it has proved to be advantageous to administer
quantities of from about 0.5 to about 50 mg, preferably from 1 to
20 mg, of active substance per body weight per day in order to
achieve effective results.
[0046] Suitable solvents are:
[0047] benzyl alcohol or optionally substituted pyrrolidones such
as 2-pyrrolidone, 1-(C.sub.2-20-alkyl)-2-pyrrolidone, in particular
1-ethylpyrrolidone, 1-octylpyrrolidone, 1-dodecylpyrrolidone,
1-isopropylpyrrolidone, 1-(s- or t- or n-butyl)-pyrrolidone,
1-hexylpyrrolidone, 1-(C.sub.2-10-alkenyl)-2-pyrrolidone such as
1-vinyl-2-pyrrolidone, 1-(C.sub.3-8-cycloalkyl)-2-pyrrolidone such
as 1-cyclohexylpyrrolidone,
1-(C.sub.1-6-hydroxyalkyl)-2-pyrrolidone,
1-(C.sub.1-6-alkoxy-C.sub.1-6-alkyl)-2-pyrrolidone such as
1-(2-hydroxyethyl)-pyrrolidone, 1-(3-hydroxypropyl)-pyrrolidone,
1-(2-methoxyethyl)-pyrrolidone, 1-(3-methoxypropyl)-pyrrolidone,
and also 1-benzylpyrrolidone. Particular mention may be made of
benzyl alcohol or n-dodecyl- or n-octylpyrrolidone. These solvents
can be employed either alone or in a mixture with additional
solvents (cosolvents).
[0048] They are present in a concentration of at least 20% by
weight, preferably from 40 to 90% by weight, particularly
preferably from 50 to 90% by weight.
[0049] Suitable additional solvents or cosolvents are: cyclic
carbonates or lactones. As such there may be mentioned: ethylene
carbonate, propylene carbonate, .gamma.-butyrolactone.
[0050] They are present in a concentration from 5.0 up to 80% by
weight, preferably from 7.5 to 50% by weight, particularly
preferably from 10 to 50% by weight.
[0051] Suitable further auxiliaries are: preservatives such as
benzyl alcohol (not required if already present as solvent),
trichlorobutanol, p-hydroxybenzoic esters, n-butanol.
[0052] Thickeners such as: inorganic thickeners such as bentonites,
colloidal silicic acid, aluminium monostearate, organic thickeners
such as cellulose derivatives, polyvinyl alcohols,
polyvinylpyrrolidones and copolymers thereof, acrylates and
methacrylates.
[0053] Colorants which may be mentioned are all colorants where use
on the animal is permitted, which may be dissolved or
suspended.
[0054] Auxiliaries are also spreading oils such as di-2-ethythexyl
adipate, isopropyl myristate, dipropylene glycol pelargonate,
cyclic and acyclic silicone oils such as dimeticones and also co-
and terpolymers thereof with ethylene oxide, propylene oxide and
formalin, fatty acid esters, triglycerides, fatty alcohols.
[0055] Antioxidants are sulphites or metabisulphites such as
potassium metabisulphite, ascorbic acid, butylated hydroxytoluene,
butylated hydroxyanisole, tocopherol.
[0056] Light stabilizers are, for example, substances from the
class of the benzophenones or Novantisol acid.
[0057] Adhesives are, for example, cellulose derivatives, starch
derivatives, polyacrylates, naturally occurring polymers such as
alginates, gelatin.
[0058] Auxiliaries are also emulsifiers such as nonionic
surfactants, for example polyoxyethylated castor oil,
polyoxyethylated sorbitan monooleate, sorbitan monostearate,
glycerol monostearate, polyoxyethylstearate, alkylphenol polyglycol
ethers;
ampholytic surfactants such as di-Na
N-lauryl-.beta.-iminodipropionate or lecithin;
anionic surfactants, such as Na-lauryl sulphate, fatty alcohol
ether sulphates, mono/dialkyl-polyglycol ether orthophosphoric
ester monoethanolamine salt;
cationic surfactants such as cetyltrimethylammonium chloride.
[0059] Further auxiliaries are agents with which the formulations
according to the invention can be sprayed or squirted onto the
skin. These are the conventional propellent gases required for
spray cans, such as propane, butane, dimethyl ether, CO.sub.2 or
halogenated lower alkanes, or mixtures thereof with one
another.
[0060] While being of low toxicity to warm-blooded species, the
formulations according to the invention are suitable for the
control of parasitic insects which are encountered in animal
keeping and animal breeding in domestic and productive animals and
in zoo and laboratory animals and animals used for experimentation
and in the pursuit of hobbies. In this context they are active
against all or individual stages of development of the pests and
against resistant and normally sensitive species of the pests.
[0061] The pests include:
from the order of the Anoplura e.g. Haematopinus spp., Linognathus
spp., Solenopotes spp., Pediculus spp., Pthirus spp.;
from the order of the Mallophaga e.g. Trimenopon spp., Menopon
spp., Eomenacanthus spp., Menacanthus spp., Trichodectes spp.,
Felicola spp., Damalinea spp., Bovicola spp;
[0062] from the order of the Diptera e.g. Chrysops spp., Tabanus
spp., Musca spp., Hydrotaea spp., Muscina spp., Haematobosca spp.,
Haematobia spp., Stomoxys spp., Fannia spp., Glossina spp., Lucilia
spp., Calliphora spp., Auchmeromyia spp., Cordylobia spp.,
Cochliomyia spp., Chrysomyia spp., Sarcophaga spp., Wohlfartia
spp., Gasterophilus spp., Oesteromyia spp., Oedemagena spp.,
Hypoderma spp., Oestrus spp., Rhinoestrus spp., Melophagus spp.,
Hippobosca spp.
From the order of the Siphonaptera e.g. Ctenocephalides spp.,
Echidnophaga spp., Ceratophyllus spp.
[0063] Particular mention may be made of the action against
Siphonaptera, especially against fleas.
[0064] The productive and breeding animals include mammals such as,
for example, cattle, horses, sheep, pigs, goats, camels, water
buffalo, donkeys, rabbits, fallow deer, reindeer, fur-bearing
animals such as, for example, mink, chinchilla or racoon, birds
such as, for example, chickens, geese, turkeys, ducks.
[0065] Laboratory animals and those for experimentation include
mice, rats, guinea pigs, golden hamsters, dogs and cats.
[0066] The hobby animals include dogs and cats.
[0067] Administration can be effected both prophylactically and
therapeutically.
[0068] In the shaped articles according to the invention, it is
also possible for further active substances to be present. The
further active substances include insecticides such as
phosphorus-containing compounds, i.e. phosphates or phosphonates,
natural or synthetic pyrethroides, carbamates, amidines, juvenile
hormones and juvenoid synthetic active substances, and chitin
synthesis inhibitors such as diaryl ethers and benzoylureas.
[0069] The phosphates or phosphonates include: [0070]
0-ethyl-0-(8-quinolyl)phenyl thiophosphate (quintiofos), [0071]
0,0-diethyl 0-(3-chloro-4-methyl-7-coumarinyl)thiophosphate
(coumaphos), [0072] 0,0-diethyl 0-phenylglycoxylonitrile oxime
thiophosphate (phoxim), [0073] 0,0-diethyl
0-cyanochlorobenzaldoxime thiophosphate (chlorphoxim), [0074]
0,0-diethyl 0-(4-bromo-2,5-dichlorophenyl)phosphorothionate
(bromophos-ethyl), [0075] 0,0,0',0'-tetraethyl
S,S'-methylene-di(phosphorodithionate) (ethion), [0076]
2,3-p-dioxanedithiol S,S-bis(0,0-diethyl phosphorodithionate),
[0077] 2-chloro-1-(2,4-dichlorophenyl)-vinyl diethyl phosphate
(chlorfenvinphos), [0078] 0,0-dimethyl
0-(3-methyl-4-methylthiophenyl)thionophosphate (fenthion).
[0079] The carbamates include: [0080] 2-isopropoxyphenyl
methylcarbamate (propoxur), [0081] 1-naphthyl N-methylcarbamate
(carbaryl).
[0082] The synthetic pyrethroides include [0083]
3-[2-(4-chlorophenyl)-2-chlorovinyl]-2,2-dimethyl-cyclo-propanecarboxylic
acid (.varies.-cyano-4-fluoro-3-phenoxy)-benzyl ester (flumethrin),
[0084] .varies.-cyano(4-fluoro-3-phenoxy)-benzyl
2,2-dimethyl-3-(2,2-dichlorovinyl)-cyclopropanecarboxylate
(cyfluthrin) and its enantiomers and stereomers, [0085]
.varies.-cyano-3-phenoxybenzyl(.+-.)-cis,trans-3-(2,2-dichlorovinyl)-2,2--
dimethylcyclopropanecarboxylate (deltamethrin), [0086]
.varies.-cyano-3-phenoxybenzyl
2,2-dimethyl-3-(2,2-dichlorovinyl)-cyclopropanecarboxylate
(cypermethrin), [0087]
3-phenoxybenzyl(.+-.)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopr-
opanecarboxylate (permethrin), [0088]
.varies.-cyano-3-phenoxy-benzyl .varies.-(p-Cl-phenyl)-isovaterate
(fenvalerate), [0089] 2-cyano-3-phenoxybenzyl
2-(2-chloro-.varies.,.varies.,.varies.-trifluoro-p-toluidino)-3-methylbut-
yrate (fluvalinate).
[0090] The amidines include: [0091]
3-methyl-2-[2,4-dimethyl-phenylimino]-thiazoline, [0092]
2-(4-chloro-2-methylphenylimino)-3-methylthiazolidine, [0093]
2-(4-chloro-2-methylphenylimino)-3-(isobutyl-1-enyl)-thiazolidine
[0094]
1,5-bis-(2,4-dimethylphenyl)-3-methyl-1,3,5-triazapenta-1,4-diene
(amitraz).
[0095] Cyclic macroliths such as invermectins and abamectins. In
this context there may be mentioned, for example,
5-0-dimethyl-22,23-dihydroavermectin-A.sub.1a,
-22,23-dihydroavermectin B.sub.1a and 22,23-dihydroavermectin
B.sub.b1 (cf. for example WHO. F. A. Series 27, pp. 27-73 (1991)).
The juvenile hormones and juvenile hormone-like substances include,
in particular, compounds of the following formulae: ##STR8##
[0096] The substituted diaryl ethers include, in particular
TABLE-US-00001 ##STR9## R.sup.1 R.sup.3 R.sup.5 R.sup.6 Z H H
CH.sub.3 H O H H CH.sub.3 2-Cl O 5-F H CH.sub.3 H O H H CF.sub.3 H
O H H C.sub.2H.sub.5 H O H H H H O H H CH.sub.3 H CH.sub.2 H H
CH.sub.3 H C(CH.sub.3).sub.2
[0097] The benzoyl ureas include compounds of the formula
TABLE-US-00002 ##STR10## R.sup.1 R.sup.2 R.sup.4 H Cl CF.sub.3 Cl
Cl CF.sub.3 F F CF.sub.3 H F CF.sub.3 H Cl SCF.sub.3 F F SCF.sub.3
H F SCF.sub.3 H Cl OCF.sub.3 F F OCF.sub.3 H F OCF.sub.3 F F
##STR11## F F ##STR12## F F ##STR13##
[0098] The triazines include compounds of the formula
TABLE-US-00003 ##STR14## R.sub.1 R.sub.2 R.sub.3 Cyclopropyl H H
Cyclopropyl H CH.sub.3 Cyclopropyl H C.sub.2H.sub.5 Cyclopropyl H
C.sub.3H.sub.7-n Cyclopropyl H C.sub.4H.sub.9-n Cyclopropyl H
C.sub.5H.sub.11-n Cyclopropyl H C.sub.6H.sub.13-n Cyclopropyl H
C.sub.7H.sub.15-n Cyclopropyl H C.sub.8H.sub.17-n Cyclopropyl H
C.sub.12--H.sub.25-n Cyclopropyl H CH.sub.2--C.sub.4H.sub.9-n
Cyclopropyl H CH.sub.2CH(CH.sub.3)C.sub.2H.sub.5 Cyclopropyl H
CH.sub.2CH.dbd.CH.sub.2 Cyclopropyl Cl C.sub.2H.sub.5 Cyclopropyl
Cl C.sub.6H.sub.13-n Cyclopropyl Cl C.sub.8H.sub.17-n Cyclopropyl
Cl C.sub.12H.sub.25-n Cyclopropyl H Cyclopropyl Cyclopropyl H
COCH.sub.3 Cyclopropyl H COCH.sub.3 HCl Cyclopropyl H
COC.sub.2H.sub.5 HCl Cyclopropyl H COC.sub.2H.sub.5 Cyclopropyl H
COC.sub.3H.sub.7-n Cyclopropyl H COC.sub.3H.sub.7-i Cyclopropyl H
COC.sub.4H.sub.9-t HCl Cyclopropyl H COC.sub.4H.sub.9-n Cyclopropyl
H COC.sub.6H.sub.13-n Cyclopropyl H COC.sub.11--H.sub.23-n
Cyclopropyl COCH.sub.3 COC.sub.2H.sub.5 Cyclopropyl
COC.sub.3H.sub.7-n COC.sub.6H.sub.13-n Cyclopropyl COCH.sub.3
COC.sub.3H.sub.7-n Cyclopropyl COC.sub.2H.sub.5 COC.sub.3H.sub.7-n
Cyclopropyl H COCyclopropyl Cyclopropyl COCyclopropyl COCyclopropyl
Cyclopropyl COCH.sub.3 COCH.sub.3 Isopropyl H H Isopropyl H
COCH.sub.3 Isopropyl H COC.sub.3H.sub.7-n Cyclopropyl H
CONHCH.sub.3 Cyclopropyl H CONHC.sub.3H.sub.7-i Cyclopropyl
CONHCH.sub.3 CONHCH.sub.3 Cyclopropyl H SCNHCH.sub.3 Cyclopropyl H
CONHCH.sub.2CH.dbd.CH.sub.2 Cyclopropyl CONHCH.sub.2CH.dbd.CH.sub.2
CONHCH.sub.2CH.dbd.CH.sub.2 Cyclopropyl CSNHCH.sub.3
CSNHCH.sub.3
[0099] Particular emphasis should be given to the further active
substances having the common names propoxur, cyfluthrin,
flumethrin, pyriproxyfen, methoprene, diazinon, amitraz, fenthion
and levamisol.
[0100] In the examples which follow, the active substance employed
is 1-[(6-chloro-3-pyridinyl)methyl]-N-nitro-2-imidazolidinium
(common name imidacloprid).
EXAMPLE 1
[0101] TABLE-US-00004 Imidacloprid 10 g Propylene carbonate 45 g
Benzyl alcohol 45 g .RTM.Belsil DMC 6031 1 g
[0102] (A polysiloxane copolymer from Wacker GmbH, D-81737
Munich)
EXAMPLE 2
[0103] TABLE-US-00005 Imidacloprid 10 g n-octyl-2-pyrrolidone 44.5
g .gamma.-butyrolactone 44.5 g .RTM.Belsil L 066 1 g
[0104] (A polysiloxane copolymer from Wacker GmbK D-81737
Munich)
EXAMPLE 3
[0105] TABLE-US-00006 Imidacloprid 8.5 g n-dodecyl-pyrrolidone
45.25 g .gamma.-butyrolactone 45.25 g .RTM.Belsil L 066 1 g
[0106] (Polysiloxane copolymer as spreading agent)
EXAMPLE 4
[0107] TABLE-US-00007 Imidacloprid 10 g Benzyl alcohol 89.9 g .RTM.
Belsil DMC 6031 0.1 g
[0108] (Polysiloxane copolymer as spreading agent)
EXAMPLE 5
[0109] TABLE-US-00008 Imidacloprid 12.5 g Benzyl alcohol 70.0 g
propylene carbonate 17.5 g
EXAMPLE 6
[0110] TABLE-US-00009 Imidacloprid 10.0 g 1-cyclohexylpyrrolidone
80.0 g Propylene carbonate 10.0 g
EXAMPLE 7
[0111] TABLE-US-00010 Imidacloprid 11.0 g Benzyl alcohol 70.0 g
Propylene carbonate 15.0 g Isopropyl myristate 4.0 g
EXAMPLE 8
[0112] TABLE-US-00011 Imidacloprid 12.5 g Benzyl alcohol 70.0 g
Propylene carbonate 17.4 g Butylated hydroxytoluene 0.1 g
EXAMPLE 9
[0113] TABLE-US-00012 Imidacloprid 10.0 g Benzyl alcohol 70.0 g
Propylene carbonate 17.5 g Di-2-ethylhexyl adipate 2.5 g
EXAMPLE 10
[0114] TABLE-US-00013 Imidacloprid 12.5 g 2-pyrrolidone 70.0 g
Propylene carbonate 17.5 g
EXAMPLE 11
[0115] TABLE-US-00014 Imidacloprid 10.0 g Pyriproxyfen 1.0 g Benzyl
alcohol 70.0 g Propylene carbonate 18.9 g Butylated hydroxytoluene
0.1 g
EXAMPLE 12
[0116] TABLE-US-00015 Imidacloprid 12.5 g Triflumuron 2.5 g Benzyl
alcohol 60.0 g Propylene carbonate 27.5 g
EXAMPLE 13
[0117] TABLE-US-00016 Imidacloprid 10.0 g Flumetrin 2.0 g Benzyl
alcohol 60.0 g Propylene carbonate 28.0 g
EXAMPLE 14
[0118] TABLE-US-00017 Imidacloprid 10.0 g Benzyl alcohol 60.0 g
Ethylene carbonate 15.0 g Propylene carbonate 15.0 g
USE EXAMPLE A
[0119] 2 ml of the formulation described in Example 1 was poured
onto the back of a dog weighing 20 kg which was infested with
fleas. The following results were obtained: TABLE-US-00018 Number
of fleas per dog Period of time Day Untreated Treated % Action -1
Infestation with 100 fleas 0 Treatment and counting 30 0 100 5, 8
Infestation with 100 fleas 9 Counting 56 0 100 15 Infestation with
100 fleas 16 Counting 76 0 100 19 Infestation with 100 fleas
(untreated animals) 250 fleas (treated animals) 20 Counting 39 0
100 26 Infestation with 100 fleas 27 Counting 43 0 100
USE EXAMPLE B
[0120] 1 ml of the solution according to Example 4 was placed on
the shoulders of a dog weighing 20 kg. The animal was infested with
200 fleas after 2 and after 6 days of treatment. On day 3 and on
day 7, respectively, of the treatment, the fleas remaining on the
dog were counted. No living fleas were found. The action was
100%.
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